It is well known from the technical literature including patents that olefins can be effectively oxidized with osmium compounds, particularly osmium tetroxide, to their corresponding diols when the reaction is carried out with catalytic amounts of osmium tetroxide and a stoichiometric amount of a strong oxidizing agent. The oxidizing agents which have been proposed and used include the alkali metal chlorates and hypochlorites, potassium ferricyanide and hydrogen peroxide. For example, in U.S. Pat. No. 2,414,385 to Milas, unsaturated compounds having an alcohol or ether group are contacted with an initially substantially anhydrous solution of hydrogen peroxide in an inert organic solvent medium in the presence of a catalyst such as an oxide of osmium. In U.S. Pat. No. 2,773,101 to Smith et al a method is shown for recovering osmium tetroxide from a process of hydroxylating an olefinic compound with hydrogen peroxide in the presence of osmium tetroxide. The patentees state, although no data or examples are given, that inorganic peroxides such as sodium and barium peroxides or organic peroxides such as tertiary butyl peroxide, tertiary butyl hydroperoxide or benzoyl peroxide can be used instead of the hydrogen peroxide. Certainly these are not all equivalent oxidizing agents since only the tertiary butyl hydroperoxide is sufficiently water soluble and/or stable to be used as the oxidation agent.
Oxidation of Os.sup.+6 to Os.sup.+8 with molecular oxygen in aqueous alkaline solutions has also been reported, thus under these conditions olefins are oxidized to their corresponding diols at a pH in the range of 8.5 - 10.5 and to oxalic acid at a pH of 12.5.
The reaction rate is slow, however, and the reaction ceases when the molar ratio of diol to osmium tetroxide exceeds 2. The same limitation applies to allyl alcohol, glycerol, acetone and formic acid.